1-(2-Bromo-5-fluorophenyl)-3,5-dimethyl-1H-1,2,4-triazole → 4-Fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile

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The title compound was prepared in 64% yield as a tan crystalline powder (HPLC: 1.31 min, AP 95% at 220 nm) from 1-(2-bromo-5-fluorophenyl)-3,5-dimethyl-1H-1,2,4-triazole and CuCN in DMF at 125-130° C. for 7 h by the method used for the preparation of 4-fluoro-2-pyrazol-1-yl-benzonitrile. An analytical sample was obtained by column purification (SiO2, 20% EtOAc/CH2Cl2), followed by trituration with Et2O. LC/MS m/z 217 (M+H). 1H NMR (CDCl3, 500 MHz) δ ppm 2.45 (3H, s, 11-Me), 2.49 (3H, s, 10-Me), 7.25 (1H, dd, J=8.5, 2.5 Hz, 3-CH), 7.31 (1H, dt, J=8.5, 2.5 Hz, 5-CH), 7.87 (1H, dd, J=8.7, 5.6 Hz, 6-CH). 13C NMR (CDCl3, 125.8 Hz) δ ppm 12.7 (10-Me), 13.8 (11-Me), 107.1 (d, J=3.8 Hz, 1-C), 114.8 (7-CN), 116.2, (d, J=25 Hz, 3-CH), 117.6 (d, J=22 Hz, 5-CH), 136.0 (d, J=10 Hz, 6-CH), 141.6 (d, J=10 Hz, 2-C), 153.9 (8-C), 161.0 (9-C), 165.0 (d, J=260 Hz, 4-CF). HRMS (ESI) calcd for C11H10FN4 (M+H) 217.0889, found 271.0879 (δ-4.8 ppm). Anal. calcd for C11H9FN4: C61.10, H4.19, N25.91; found C60.78, H3.93, N26.05.

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